Backed by Y Combinator and a16z.
About the role
Lead the design and implementation of critical systems that serve as building blocks for the platform Make architectural decisions that optimize for scale, performance, and maintainability
What they're looking for
- Have 8+ years of experience building and scaling complex software systems
- Have led architecture or technical strategy for a product or platform team
- Are comfortable working across backend, data, and infra layers (and diving into frontend when needed)
- Think in systems and excel at finding pragmatic solutions to messy problems
- Are excited to shape the technical direction of a growing company
- Have strong communication skills and enjoy working across disciplines
More about this role
Chestnut is building the first AI-native operating system for insurance distribution by transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution.
Backed by a16z, we’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding.
This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency.
At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount.
If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your...
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